Dimethylformamide → HCID 14834217, compound

HRID 477005Notes

Reaction equation

HRID 477005 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.C(OP([CH2:18]/[CH:19]=[CH:20]/[C:21]([O:23][CH3:24])=[O:22])(OCC)=O)C.[H-].[Na+].CN(C)C=O>O1CCCC1.O>[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1/[CH:4]=[CH:18]/[CH:19]=[CH:20]/[C:21]([O:23][CH3:24])=[O:22]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 69962-ChlorobenzaldehydeHCID 24758Sodium hydrideHCID 5872654HCID 5872654, compound

Product 1

HCID 14834217HCID 14834217, compoundYield 82.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 500 mg of o-chlorobenzaldehyde and 840 mg of methyl 4-diethylphosphonocrotonate dissolved in 5 ml of tetrahydrofuran, 142 mg of sodium hydride (60% oily dispersion) was added under ice-cooling. Imeediately, 2 ml of dimethylformamide was added and the mixture was stirred at room temperature for 2 hours. The mixture was poured into water and extracted twice with ether. The organic layer was washed twice with water, dried and the solvent was removed by distillation. The residue was purified by silica gel column chromatography (solvent: hexane-ethyl acetate=20:1) to give 650 mg of methyl (2E, 4E)-5-(2-chlorophenyl)-2,4-pentadienoate as an oily substance.

Workup

  1. temperaturecooling
  2. extractionextracted twice with ether
  3. washThe organic layer was washed twice with water
  4. customdried
  5. customthe solvent was removed by distillation
  6. customThe residue was purified by silica gel column chromatography (solvent: hexane-ethyl acetate=20:1)

Sources & evidence

ORD record
ord-df498ee32ba14ad99bd336ce44c1957c
Source dataset
uspto-grants-1989_12
Patent number
US04886817

Reaction notes

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